I have made up two pairs of similar sentences below.

(1a) My old shoes brought back my memory of the time someone stole my watch.

(1b) My old shoes brought back a memory of the time someone stole my watch.

(2a) The song brought back my memory of my dad who passed away ten years ago.

(2b) The song brought back a memory of my dad who passed away ten years ago.

If I am talking about one specific incident, do I use "my memory" or "a memory"? Thanks for your help.

Original Post

Hi, Ansonman,

The phrase is "bring back memories" (in the plural). If the speaker needs to make clear that those memories came back to him/her rather than to an unidentified person or group of people, then an object pronoun rather than a possessive determiner should be used:

1c) My old shoes brought me back memories of the time someone stole/had stolen my watch. (Note: I find it hard to see the connection between the shoes and the watch, but it's just a narrative detail.)

Actually, I'd prefer the passive in the relative clause:

1d) My old shoes brought me back memories of the time my watch was/had been stolen.

2c) The song brought me back memories of my dad, who passed away ten years ago/who had passed away ten years before/earlier.

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